US4328367A - Tetrahydrophthalamide derivatives - Google Patents

Tetrahydrophthalamide derivatives Download PDF

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US4328367A
US4328367A US05/963,762 US96376278A US4328367A US 4328367 A US4328367 A US 4328367A US 96376278 A US96376278 A US 96376278A US 4328367 A US4328367 A US 4328367A
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carbon atoms
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formula
alkyl
compound
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Hiroshi Nagase
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Takeda Pharmaceutical Co Ltd
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Takeda Chemical Industries Ltd
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Priority claimed from JP14367277A external-priority patent/JPS6023668B2/ja
Priority claimed from JP13301578A external-priority patent/JPS5559153A/ja
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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/44—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
    • A01N37/46—N-acyl derivatives
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
    • A01N37/30—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof containing the groups —CO—N< and, both being directly attached by their carbon atoms to the same carbon skeleton, e.g. H2N—NH—CO—C6H4—COOCH3; Thio-analogues thereof
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/34—Nitriles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
    • A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
    • A01N41/10—Sulfones; Sulfoxides
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
    • A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
    • A01N43/08—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings with oxygen as the ring hetero atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/52—Radicals substituted by nitrogen atoms not forming part of a nitro radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/87—Benzo [c] furans; Hydrogenated benzo [c] furans
    • C07D307/90—Benzo [c] furans; Hydrogenated benzo [c] furans with an oxygen atom in position 1 and a nitrogen atom in position 3, or vice versa

Definitions

  • This invention relates to novel tetrahydrophthalamide derivatives of the general formula: ##STR2## wherein X is chlorine or bromine, and R is hydrogen or an alkyl, a substituted alkyl, a cycloalkyl, a substituted cycloalkyl, an alkenyl or an alkynyl group, which have herbicidal activity, to methods of producing the same and preparations containing the same.
  • the compounds (I) are highly effective against annual and perennial grasses or weeds and can be used as herbicides effectively in the paddy-fields or/and upland crop lands.
  • Grasses and weeds sensitive to these compound (I) are: in paddy fields annual monocotyledonous plants such as barnyard grass Echinochloa oryzicola Vasing., umbrella plant Cyperus difformis L., monochoria Monochoria vaginalis PRESL., etc., annual dicotyledonous plants such as false pimpernel Lindernia procumbens Philcox, toothcup Rotala indica KOEHNE, etc. and perennial weeds such as spike rush Eleocharis acicularis Roem, et Schult., Sagittaria pygmaea Miq., Cyperus serotinus Rottb., Scirpus juncoides Roxb. var.
  • amurensis Ohwi, annual blue grass Poa annua L., etc and annual dicotyledonous plants such as common chickweed Stellaria media Vill., pig weeds Amaranthus retroflexus L., lamb's quarters Chenopodium album L., inutade Polygonum Blumei Meisn. and common purslane Portulaca oleracea L., Sida spinosa L., Abutilon theophrasti Medic., Xanthium strumarium L. and perennial weeds such as Sorghum halpense Pers.
  • the compounds (I) can be applied both in the pre-emergence and in post-emergence states.
  • the alkyl group is a straight-chain or branched alkyl group such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec.-butyl, tert.-butyl, pentyl, isopentyl, hexyl, heptyl, octyl, nonyl, decyl, lauryl or stearyl, alkyls containing 1 to 10 carbon atoms being particularly preferred.
  • substituted alkyl group there may be mentioned alkyl groups which are substituted, for example by hydroxyl, cyano, halogen (e.g. chlorine, bromine, etc.), carboxyl, straight-chain or branched alkoxy groups of 1 to 8 carbon atoms (e.g. methoxy, ethoxy, isopropoxy, n-propoxy, etc.), alkoxycarbonyl groups of 1 to 4 carbon atoms (e.g. ethoxycarbonyl, etc.), acyloxy groups of 1 to 10 carbon atoms (e.g.
  • acetoxy, propionyloxy, benzoyloxy, etc. furyl which may optionally be substituted, for example by nitro, halogen or lower alkyl of 1 to 3 carbon atoms, groups represented by the general formula: ##STR3## [wherein Y is hydrogen, halogen, lower alkyl, lower alkoxy, nitro or hydroxyl; n is an integer of 1, 2 or 3], or groups represented by the general formula:
  • R 1 is a straight-chain or branched alkyl group of 1 to 5 carbon atoms; m is an integer of 0, 1 or 2]
  • the halogen is preferably chlorine or bromine
  • the lower alkyl is preferably an alkyl group of 1 to 3 carbon atoms
  • the lower alkoxy is preferably an alkoxy group of 1 to 3 carbon atoms.
  • the group (VIII) is preferably an unsubstituted phenyl group or a phenyl group substituted by one or two substituents such as chlorine or methyl.
  • the group (IX) there may be mentioned ethylthio, n-propylthio, n-butylthio, ethylsulfinyl, ethylsulfonyl, n-propylsulfinyl, n-propylsulfonyl and n-butylsulfonyl.
  • Especially desirable substituted alkyls are such that the alkyl moiety thereof is a straight-chain alkyl group of 1 to 4 carbon atoms.
  • the substituted alkyl may have two or more substituents which may be the same substituent group of different groups.
  • cycloalkyl group there may be mentioned alkyls of 3 to 8 carbon atoms, preferably of 3 to 6 carbon atoms, such as cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl.
  • substituted cycloalkyl group there may be mentioned said cycloalkyl groups which are substituted, for example by lower alkyl groups having 1 to 4 carbon atoms or halogen (e.g. chlorine, bromine, etc.).
  • the alkenyl group is an alkenyl containing 2 to 8 carbon atoms, preferably 3 to 6 carbon atoms, such as allyl, methallyl, pentenyl, butenyl or hexenyl.
  • the alkynyl group is an alkynyl containing 2 to 8 carbon atoms, preferably 3 to 6 carbon atoms, such as propargyl. These alkenyls or alkynyls may be optionally substituted, for example, by a phenyl group.
  • the compound (III) is a primary amine
  • this may be employed either as the free base or in the form of a salt which does not affect the reaction.
  • a salt of the primary amine (III) there may be mentioned the salts with hydrogen halides, e.g. hydrogen chloride, hydrogen bromide, etc. and with inorganic or organic acids such as sulfonic acid, nitric acid, oxalic acid, acetic acid and so forth.
  • the compound (III) is ammonia, it may be employed in a gaseous state or in a solution of a suitable solvent.
  • the reaction is normally carried out using about 1 to several moles, preferably about 1 to 1.2 moles, of the compound (III) to each mole of compound (II).
  • the reaction is desirably conducted in an inert solvent such as a hydrocarbon (e.g. benzene, toluene, hexane, cyclohexane, etc.), a halogenated hydrocarbon (e.g. dichloromethane, carbon tetrachloride, chlorobenzene, etc.), diethyl ether, dioxane, tetrahydrofuran, acetonitrile, acetone, methyl ethyl ketone, ethyl acetate, nitrobenzene or the like.
  • the reaction is normally conducted at about 5° C. to about 60° C. and preferably between 20° C. and 40° C. Normally, the reaction time is about 5 minutes to about 10 hours and, desirably, 10 minutes to one hour.
  • the compound (I) thus obtained can be isolated and purified by conventional procedures, such as concentration, concentration under reduced pressure, extraction with a solvent, phasic transfer, crystallization, recrystallization and chromatography.
  • the tetrahydrophthalamide derivative (I) can also be produced by reacting a tetrahydroisophthalimide compound of the general formula: ##STR5## wherein R is as defined hereinbefore, with an amine of the general formula: ##STR6## wherein X is as defined hereinbefore.
  • the amine (V) may be employed as the free base or in the form of a salt such as those mentioned in connection with (III). Generally this reaction may be conducted under the conditions set forth in connection with the reaction of compound (II) with the compound (III). Thus, the proportions of reactions, solvent, temperature, time, isolation procedures and other parameters may be selected from among those mentioned.
  • the tetrahydrophthalamide derivative (I) may also be synthesized by the following method which comprises reacting a tetrahydrophthalamic acid directly with a primary amine with the elimination of water: ##STR7## wherein the symbols are as previously defined, or by the following method which comprises reacting a tetrahydrophthalamic acid ester with a primary amine: ##STR8## wherein X and R are as previously defined; and R" is a hydrocarbon residue different from R.
  • Tetrahydrophthalamide derivatives (I) wherein R is alkylsulfinylalkyl or alkylsulfonylalkyl can also be synthesized by subjecting tetrahydrophthalamide derivatives (I) having an alkylthioalkyl group as the symbol R in the formula (I) to oxidation with, for example, m-chloroperbenzoic acid or hydrogen peroxide.
  • Tetrahydrophthalamide derivatives (I) wherein R is acyloxyalkyl can also be synthesized by subjecting tetrahydrophthalamide derivatives (I) having a hydroxyalkyl group as the symbol R in the formula (I) to acylation with a suitable acylating agent, for example, acetyl chloride.
  • a suitable acylating agent for example, acetyl chloride.
  • N-(2-fluoro-4-chlorophenyl)-3,4,5,6-tetrahydroisophthalimide which falls within the scope of starting material (II) for the purposes of this invention, has been disclosed in U.S. Pat. No. 3,990,880, and other compounds of general formula (II) and compounds of general formula (IV) can be produced, for example by the method described in the above-mentioned patent, a method analogous thereto or a method which may be schematically shown as follows: ##STR9## In the above formulae, X and R are as previously defined.
  • the tetrahydrophthalamic acids (VI) and (VII) can be produced by the processes schematically shown above, i.e. by reacting 3,4,5,6-tetrahydrophthalic anhydride with an amine in substantially equimolar proportions in an inert solvent, normally at 10° to 90° C. and preferably at 20° to 60° C., for 5 minutes to one hour.
  • inert solvent there may be mentioned benzene, toluene, hexane, dichloromethane, carbon tetrachloride, chlorobenzene, diethyl ether, dioxane, tetrahydrofuran, acetonitrile, acetone, methyl ethyl ketone, ethyl acetate and nitrobenzene. While both compounds (VI) and (VII) may be isolated and purified by procedures known per se, they may be directly subjected to dehydrative cyclization into compounds (II) and (IV), respectively, with the advantage that isolation and purification procedures are avoided.
  • the dehydrative cyclization of 3,4,5,6-tetrahydrophthalamic acid (VI) or (VII) is advantageously conducted in an inert solvent using a dehydrative-condensing agent.
  • a dehydrative-condensing agent there may be mentioned carbodiimides such as dicyclohexylcarbodiimide, diethylcarbodiimide, etc., combinations of bases with acylating agents and combinations of bases with acid halide-forming agents.
  • bases there may be mentioned tertiary organic amines such as pyridine, quinoline, dimethylaniline, triethylamine, trimethylamine, etc.
  • alkali metal carbonates and bicarbonates such as sodium carbonate, sodium hydrogen carbonate, potassium carbonate, etc.
  • chlorocarbonic acid esters e.g. methyl chlorocarbonate, ethyl chlorocarbonate, etc.
  • benzoyl chloride examples of said acid halide-forming agents may for example be phosgene, thionyl halide (e.g. thionyl chloride, thionyl bromide, etc.) and phosphorus oxychloride.
  • the proportion of said dehydrative-condensing agent is normally about 1 to 2 moles and preferably about 1 to 1.2 moles based on each mole of compound (VI) or (VII).
  • the reaction is normally conducted at about 0° C. to about 50° C.
  • the reaction is normally carried out at about -15° C. to about 60° C.
  • the reaction time is normally in the range of about 30 minutes to about 3 hours.
  • the inert solvent employed in this dehydrative-cyclization reaction may for example be a hydrocarbon (e.g. benzene, toluene, hexane, cyclohexane, etc.), a halogenated hydrocarbon (e.g.
  • the compound of this invention (I) may be used for weed control purposes, as follows.
  • a liquid carrier e.g. a solvent
  • an appropriate solid carrier e.g. a diluent or vehicle
  • an emulsifier, suspending agent, extender, penetrant, wetting agent, viscosity builder, stabilizer or/and other additives if necessary, are formulated into such application forms as an oil solution, emulsifiable concentrate, wettable powder, dust, granules, tablets, aerosol mist or ointment.
  • concentration of the active component compound or compounds in such a herbicidal composition varies with the intended application, it is suitable to employ about 10 to 90 weight percent in the case of emulsifiable concentrates or wettable powders, for instance; about 0.1 to 10 weight percent in the case of oil solutions and dusts; and about 1 to 20 weight percent in the case of granules. It should, however, be understood that deviations from the above-indicated range are permissible depending upon the intended application. In using the emulsifiable concentrates and wettable powders, these preparations are advantageously applied as diluted with a diluent such as water to a suitable concentration (e.g. 100 to 100000-fold).
  • a suitable concentration e.g. 100 to 100000-fold
  • liquid carrier for use in the preparation of the present herbicidal compositions
  • water e.g. methanol, ethanol, ethylene glycol, etc.
  • ketones e.g. acetone, methyl ethyl ketone, etc.
  • ethers e.g. dioxane, tetrahydrofuran, cellosolve, etc.
  • aliphatic hydrocarbons e.g. gasoline, kerosene, fuel oil, machine oil, etc.
  • aromatic hydrocarbons e.g.
  • the solid carrier may for example be any or a mixture of such carriers as vegetable powders (e.g.
  • soybean meal e.g. kaolin, bentonite, acid clay and other clays; talc powder, agalmatolite and other varieties of talc; diatomaceous earth, mica powder and other forms of silica), alumina, flowers of sulfur, activated carbon and so on.
  • mineral powders e.g. kaolin, bentonite, acid clay and other clays; talc powder, agalmatolite and other varieties of talc; diatomaceous earth, mica powder and other forms of silica
  • talc powder e.g. kaolin, bentonite, acid clay and other clays
  • talc powder e.g. kaolin, bentonite, acid clay and other clays
  • talc powder e.g. kaolin, bentonite, acid clay and other clays
  • talc powder e.g. kaolin, bentonite, acid clay and other clays
  • talc powder e.g. kaolin, benton
  • bases for said ointment there may be employed, among others, polyethylene glycol, pectin, polyhydric alcohol esters of higher fatty acids (e.g. glyceryl monostearate), cellulose derivatives (e.g. methyl-cellulose), sodium alginate, bentonite, higher alcohols (e.g. glycerol and other polyhydric alcohols), vaseline, petrolatum album, liquid paraffin, lard, vegetable oils, lanolin, dehydrated lanolin, hydrogenated oil, waxes, resins and so forth.
  • These ointment bases may be employed alone or as a mixture, with or without the addition of surfactants or other additives.
  • soaps for emulsifiers, extenders, penetrants, dispersing agents, etc.
  • polyoxyalkylaryl esters e.g. Nonal®, Takemoto Yushi K.K.
  • alkylsulfates e.g. Emal 10®, Emal 40®, Kao Atlas K.K.
  • alkylsulfonates e.g. Neogen®, Neogen T®, Daiichi Kogyo Seiyaku K.K., Neopelex®, Kao Atlas K.K.
  • polyethylene glycol ethers e.g.
  • Nonipol 85® Nonipol 100®, Nonipol 160®, Sanyo Kasei K.K.
  • polyhydric alcohol esters e.g. Tween 20®, Tween 80®, Kao Atlas K.K.
  • the compound (I) is applied in the amount of about 1 to about 50 g, preferably about 2 to about 40 g, per are of a paddy-rice field or about 1 to about 50 g, preferably about 2 to about 40 g, per are of a dry field.
  • the compound (I) is used as a pre-emergence herbicide.
  • the compound (I) is low in toxicity to mammalian animals and fishes, thus being suited for use in agricultural applications.
  • herbicidal compositions containing the compound (I) there may be further incorporated other herbicides, plant growth regulators, fungicides (e.g.
  • organochlorine fungicides organosulfur fungicides, antibiotics, etc.
  • insecticides e.g organophosphorus insecticides, natural insecticides, etc.
  • miticides e.g organophosphorus insecticides, natural insecticides, etc.
  • miticides e.g organophosphorus insecticides, natural insecticides, etc.
  • miticides e.g organophosphorus insecticides, natural insecticides, etc.
  • miticides e.g organophosphorus insecticides, natural insecticides, etc.
  • miticides e.g organophosphorus insecticides, natural insecticides, etc.
  • miticides e.g organophosphorus insecticides, natural insecticides, etc.
  • miticides e.g organophosphorus insecticides, natural insecticides, etc.
  • miticides e.g organophosphorus insecticides, natural insecticides, etc.
  • miticides e.g organophosphorus insecticide
  • 2-fluoroaniline was acetylated with acetic anhydride to obtain 2-fluoroacetanilide.
  • This 2-fluoroacetanilide was held in glacial acetic acid at 43°-52° C. and an equivalent of chlorine gas was introduced, whereby 2-fluoro-4-chloroacetanilide was obtained.
  • This product was deacetylated with hydrochloric acid and neutralized with sodium hydroxide to recover 2-fluoro-4-chloroaniline as an oil boiling at 64°-65° C./0.25 mmHg.
  • N-(2-fluoro-4-bromophenyl)-3,4,5,6-tetrahydroisophthalamic acid 84.4 g
  • dicyclohexylcarbodiimide 51.0 g
  • the precipitate was removed and the filtrate was concentrated to dryness under reduced pressure.
  • the oil was washed with n-hexane by decanting.
  • the crystals were recovered by filtration and washed with a small quantity of cold n-hexane. Yield 36.4 g.; m.p. 45°-46° C.
  • a wettable powder product comprising a milled mixture of 30 weight % of N-isopropyl-N'-(2-fluoro-4-chlorophenyl)-3,4,5,6-tetrahydrophthalamide, 5 weight % of sodium ligninsulfonate, 5 weight % of polyethylene glycol ether (Nonipol 85®) and 60 weight % of clay.
  • a granular preparation product comprising, as kneaded with water and granulated, 10 weight % of N-octyl-N'-(2-fluoro-4-chlorophenyl)-3,4,5,6-tetrahydrophthalamide, 5 weight % of sodium ligninsulfonate and 85 weight % of bentonite.
  • An emulsifiable concentrate comprising 20 weight % of N-propyl-N'-(2-fluoro-4-bromophenyl)-3,4,5,6-tetrahydrophthalamide, 75 weight % of xylene and 5 weight % of polyethylene glycol ether (Nonipol 85®.)
  • Biscuit-fired pots 9 cm across, were each filled with tilled land soil and, after sowing the pot with seeds of crabgrass Digitaria adscendens HENR., pigweed Amaranthus retroflexus L. and Glycine max Merrill (soybean), a layer, 0.5 cm thick, of cover soil was applied. Then, using a spray gun, the surface of the soil was evenly sprayed with a dilution of the emulsifiable concentrate containing various compounds represented by formula (I). The emulsifiable concentrate was diluted with 10 l of water to provide 4 g, 10 g or 40 g active component per are. After 21 days, the effects and injuries to the plants were investigated. The herbicidal effects are expressed according to the following index system.
  • the injuries to soybean plants are expressed according to the following index system.
  • Plastic pots 900 cm 2 , were respectively filled with tilled land soil and sown with seeds of crabgrass Digitaria adscendensHENR., pigweed Amaranthus retroflexus L., lamb's quarters Chenopodium album L., inutade Polygonum Blumei Meisn., common purslane Portulaca oleracea L., maize Zea Mays L., soybean Glycine Max Merr. and cotton Gossypium hirsutum L. followed by the laying of cover soil in a thickness of 0.5 cm.

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  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Plant Pathology (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Indole Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
US05/963,762 1977-11-29 1978-11-27 Tetrahydrophthalamide derivatives Expired - Lifetime US4328367A (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
JP52-143672 1977-11-29
JP14367277A JPS6023668B2 (ja) 1977-11-29 1977-11-29 テトラヒドロフタラミド誘導体，その製造法および製剤
JP53-133015 1978-10-27
JP13301578A JPS5559153A (en) 1978-10-27 1978-10-27 Tetrahydrophthalamide derivative, its synthesis and medicinal preparation

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US (1) US4328367A (de)
CH (1) CH636345A5 (de)
DE (1) DE2851379A1 (de)
FR (1) FR2409983A1 (de)
GB (1) GB2009150B (de)
IL (1) IL56012A (de)
IT (1) IT7869726A0 (de)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5506190A (en) * 1992-03-25 1996-04-09 Sagami Chemical Research Center Tetrahydrophthalamide derivative, intermediate for producing the same, production of both, and herbicide containing the same as active ingredient
US6656971B2 (en) 2001-01-25 2003-12-02 Guilford Pharmaceuticals Inc. Trisubstituted carbocyclic cyclophilin binding compounds and their use
US20030232815A1 (en) * 1999-09-08 2003-12-18 Hamilton Gregory S. Non-peptidic cyclophilin binding compounds and their use
CN100462352C (zh) * 2001-07-10 2009-02-18 4Sc股份公司 用作抗炎、免疫调节及抗增殖药剂的新化合物

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US7365094B2 (en) 2002-12-23 2008-04-29 4Sc Ag Compounds as anti-inflammatory, immunomodulatory and anti-proliferatory agents
US7071355B2 (en) 2002-12-23 2006-07-04 4 Sc Ag Compounds as anti-inflammatory, immunomodulatory and anti-proliferatory agents
UA108760C2 (uk) 2010-07-01 2015-06-10 Кальцієві солі сполуки як протизапальні, імуномодулюючі та антипроліферативні засоби
WO2019175396A1 (en) 2018-03-16 2019-09-19 Immunic Ag Novel calcium salt polymorphs as anti-inflammatory, immunomodulatory and anti-proliferatory agents

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US5506190A (en) * 1992-03-25 1996-04-09 Sagami Chemical Research Center Tetrahydrophthalamide derivative, intermediate for producing the same, production of both, and herbicide containing the same as active ingredient
US5554581A (en) * 1992-03-25 1996-09-10 Sagami Chemical Research Center Tetrahydrophthalamide derivative, intermediate for producing the same, production of both, and herbicide containing the same as active ingredient
US20030232815A1 (en) * 1999-09-08 2003-12-18 Hamilton Gregory S. Non-peptidic cyclophilin binding compounds and their use
US6677376B1 (en) 1999-09-08 2004-01-13 Guilford Pharmaceuticals, Inc. Non-peptidic cyclophilin binding compounds and their use
US6656971B2 (en) 2001-01-25 2003-12-02 Guilford Pharmaceuticals Inc. Trisubstituted carbocyclic cyclophilin binding compounds and their use
CN100462352C (zh) * 2001-07-10 2009-02-18 4Sc股份公司 用作抗炎、免疫调节及抗增殖药剂的新化合物

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DE2851379A1 (de) 1979-05-31
GB2009150A (en) 1979-06-13
FR2409983A1 (fr) 1979-06-22
GB2009150B (en) 1982-08-18
FR2409983B1 (de) 1983-07-29
IT7869726A0 (it) 1978-11-28
CH636345A5 (de) 1983-05-31
IL56012A (en) 1983-07-31

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